Vetiver and Derivatives
Vetiver and Derivatives
Vetiver and Derivatives
V
etiver is an important woody note in perfumery. The word vetiver, vetyver in French, originated in
Tamil:* vettiveru = vetti, worthless + veru, useless.1 The Indian term for vetiver is Khus, and in
30 Indonesia is known as Akar Wangi.
source gives the yield of air-dried vetiver Java oil seemed to consist of a mixture of primary
Java roots as 2 to 3 percent.3 alcohols in which a tricyclid alcohol predomi-
The following types of vetiver oil are nates, while bicyclic alcohols amounted only to 10
available commercially: percent.
Chemical Composition
The chemical composition of vetiver oil In 1976, a study of the carbonyls of Haitian vetiver
was studied in the beginning of the 20th oil was done. Seven novel sesquiterpenoid and norses-
century. Theulier studied the physico- quiterpenoid carbonyls were characterized. The major
chemical properties of fractionated vetiver isomer of dihydro β-vetivone had “a strong rich woody
oils distilled in France and on Réunion peppery odor,” while the remaining novel carbonyls
Island. Other investigations were carried were of a general woody type odor. The researchers
out by various researchers, among them believed that all of the carbonyls play a role in achieving
Semmler.4 In the 1950s, the following com- the complex woody odor of vetiver oil.6
ponents of vetiver oil were identified:5 Among vetiver oil components characterized in
the early 1970s were α- and β-vetivones, the nors-
A language spoken by members of the Dravidians, an
* esquiterpene khusimone and three biogenetically
ethnic group from southeastern India and Ceylon. derived C-12 ketones, which were deemed to be the
most interesting. Spiroketone and khusim- Using flashchromatography, two olfactory important
one appear to play an important role in the fractions were obtained: (1) medium polar (hydrocar-
reconstruction of vetiver oil. Therefore, bons, ethers and ketones), and (2) polar alcohols and
total new syntheses of these compounds α,β-unsaturated ketones. The combination of distilla-
were developed.7 tion and repeated FC yielded several new compounds.
In the study of vetiver oils of different In the medium polar fraction, one of the sesquiter-
geographical origins, other researchers re- pene hydrocarbons that never isolated before in veti-
ported 95 compounds in the hydrocarbon- ver oil was cis-eudesmadiene. Among other isolated
rich section, fractionated via distillation of ethers were α-agarofuran and 4,7-epoxy spirovetiva-
vetiver oil Haiti, and suggested that more 1,11(12)-diene.
than 150 components were present in the In the polar fraction, the transformation of second-
total vetiver oil.8 ary alcohols to methyl ethers; subsequent split tube
In 1977, a synthesis of β-vetivone via distillation gave 30 new sesquiterpene ethers after
base-catalyzed spiroannelation of pheno- repeated FC. Olfactory comparison of the odor of
lic tosylates was reported.9 A 1978 patent several methyl ethers and their corresponding alcohols
covered a new synthesis of khusimone.10 showed that the odor of the methyl ethers was more
6,6,7-Trimethyl-tricyclo [5.2.2.01,5] undec- earthy, khusimone-vetiver or patchouly-like, while the
32 8-en-2-one was given as the starting mate- alcohols had woody odor tonalities with amber, sweet
rial for this synthesis. This compound was and grapefruit undertones.12
described as having a woody, sandalwood-
like odor with vetiver nuances, thus being Synthetic Compounds
of interest. In 1989, another synthesis of Vetiver has a lasting woody odor with a hint of cam-
khusimone was reported, starting from phoraceous, earthy and musty undertones. It has
(S)-6,6-dimethyl-5-methoxycarbonylmethyl- points in common with violet-orris and patchouli type
2-cyclohexen-1-one. Overall yield was 6.9 odors, and it blends well with sandalwood and rose
percent.11 odors. Vetiver is especially effective with musky odors.
In 1996, an analysis of vetiver Haiti Several of the modifiers of vetiver odor are listed in T-1.
was reported that showed that the main
constituents were isovalencenol, β-vet- Vetiver Imitations
ivone and khusimol. Because vetiver was Because of the complexity of vetiver oil it is difficult
a very complex oil, it is a difficult task to to reproduce the vetiver odor. Several early imitations
separate and elucidate the structure of its were developed; some served in the past to fraud the
VOL. 29 MAY 2004
labdanum absolute 40
isobutyl benzoate 12
coumarin 25
tuberose absolute 20
heliotropin 90
mimosa absolute 18
vanillin 20
ionone a 20
musk ketone 50
methoxyacetophenone 30
aldehyde C-11 10% 75
aldehyde C-12 (MNA) 10% 6
aldehyde C-10 10% 75
sandalwood EI 60
aldehyde C-12 (MNA) 10% 50
1000
1205
I
n the first part of this article (Perfumer & Flavorist, May 2004),* I discussed various vetiver types, the com-
position of vetiver oils of different origin, showed a few early vetiver imitations and illustrated a number of
traditional perfume compounds. In this article, I shall exemplify additional types of traditional perfume
46 compounds containing vetiver or its derivatives.
10 patchouly
200 bergamot
10 solvent
80 benzoin resinoid
500
50 vanillin
40 vetiver
Lavender Water1
32 coumarin
500 lavender oil French 35 musk ambrette
50 lavender absolute
25 lemon c.p.
150 bergamot
16 castoreum resinoid
30 musk Tonkin infusion 3%
8 patchouly
20 civet infusion 3%
486
10 neroli bigarade
20 orange flower absolute
20 petitgrain Grasse Origan Base No. 2903
30 orange oil sweet 200 Raldeine D Giv.
50 vetiveryl acetate 100 cassie synthetic No. 133
5 Tonka resinoid 100 vetiver Java
5 hydroxycitronellal 80 carnation synthetic No. 117
5 clary sage 45 rose synthetic No. 163
5 estragon oil 40 ylang Bourbon
PERFUMER & FLAVORIST
Rose V5
phenyl ethyl alcohol 425 cm3
rhodinol 400 cm3
jasmin synthetic 50 cm3
nerol 25 cm3
vetiver 15 cm3
sandalwood 10 cm3
neroli oil 10 cm3
tuberose oil 10 cm3
rose oil 10 cm3
Vetiver Compound6
vetiver Java 140 g
vetiver Bourbon 200 g
sandalwood 100 g
hydroxycitronellal 120 g
cinnamic alcohol 60 g
jasmin synthetic 90 g
heliotropin 80 g
coumarin 50 g
musk ketone 50 g
musk ambrette 10 g
note with herbal, cinnamic and woody Arpège (Lanvin), Chanel No. 5 (Chanel), Femme (Ro-
PERFUMER & FLAVORIST
chas), Miss Dior (Dior), Shalimar (Guerlain), Cravache
(Piguet), L’O (Lancôme), Mystère de Rochas, Bales-
tra (ICR), Anais Anais (Cacherel), Silences (Jacomo),
Sheherazade (J. Deprez), Bois des Iles de Chanel
(1920s, reappeared in 1993), Paradox (Jacomo), Tiffany
(Tiffany & Co.), Paco Energy (Paco Rabanne), Must
(Cartier), Eau de Vetiver (Guerlain), L’Eau Cheap et
Chic (Moschino), Coriolan (Guerlain), Tiffany for Men
Sport Cologne, and the 2004 fragrance Le Baiser du
Dragon (Cartier).
Conclusion
Vetiver and its derivatives are likely to remain im-
portant woody note components in a broad spectrum
of men’s and women’s fragrances in the foreseeable
future. In spite of the pessimistic prognosis of G. and
F. Robert, who include vetiver oil among the vanish-
ing raw materials because of its popularity and huge
51
world consumption of natural products, vetiver oil
is still available and used in fragrances released in
2004.15 Vetiver will continue to remain an important
ingredient because it is difficult to replace/substitute.
The newer vetiver specialties approximate the initial
vetiver odor, but leave much to be desired in compari-
son to vetiver oil’s lasting fixative power.
Address correspondence to Danute Pajuajis Anonis, 98-41 64th Road,
Rego Park, NY 11374.
References
3. Ibid., p.180
4. Jellinek, p.76
10. Ibid., p. 24
11. Ibid., p. 26
13. W.L. Schreiber, J.N. Siano and E.J. Shuster, U.S. Patents: 4,076,749;
Feb. 28, 1979; 4,107,066; Aug. 15, 1978; 4,108,799; Aug. 22, 1978 and
4,156,695; May 29, 1979; all assigned to International Flavors and
Fragrances, Inc., cf Fragrances and Flavors. Recent Developments.
Chemical Technology Review, ibid., pp. 110-114.
14. R.S. De Simone, U.S. Patent 4,146,507; March 27, 1979; assigned
to Polak’s Frutal Works.